HuagongsheHuagongshe Chemistry Print Report · For research reference only
Lithium Hydroxide → (1R*,2R*,5S*,6R*)-8-Benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-6-(2-carboxymethyl-2H-tetrazol-5-yl)-1-phenyl-8-azabicyclo[3.2.1]octane
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | (1R*,2R*,5S*,6R*)-8-Benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-6-(1-methoxycarbonylmethyl-1H-tetrazol-5-yl)-1-phenyl-8-azabicyclo[3.2.1]octane | HCID 86586756 | — |
| Solvent | Water | HCID 962 | — |
| Product | (1R*,2R*,5S*,6R*)-8-Benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-6-(2-carboxymethyl-2H-tetrazol-5-yl)-1-phenyl-8-azabicyclo[3.2.1]octane | HCID 86586757 | 94% |
Reaction Steps
Lithium hydroxide (40 mg, 0.9 mmol) was added to a solution of (1R*,2 R*,5S*,6R*)-8-benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-6-(2-methoxycarbonylmethyl-2H-tetrazol-5-yl)-1-phenyl-8-azabicyclo[3.2.1]octane (Example 144a; 0.6 g, 0.91 mmol) in water (5 ml) and THF (5 ml). The reaction mixture was stirred at room temperature for 30 minutes then partitioned between 5% citric acid solution and ethyl acetate. The organic layer was separated, dried (MgSO4), filtered and concentrated to yield the title compound (0.55 g, 94%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06727249B2 |
| Source dataset | uspto-grants-2004_04 |
| ORD ID | ord-30435fdfb8c046b18293247f143d3f62 |
| Source note | uspto-grants-2004_04 |